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2. Hoyer, D., Bell, G. I., Berelowitz, M., Epelbaum, J., Feniuk, W., Humphrey, P. P. A., O'Carroll, A-M., Patel, Y. C., Schonbrunn, A., Taylor, J. E., Reisine, T.; TIPS, 1995, 16, 86.
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Hoyer, D.1
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Humphrey, P.P.A.6
O'Carroll, A.-M.7
Patel, Y.C.8
Schonbrunn, A.9
Taylor, J.E.10
Reisine, T.11
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0028909323
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(b) Reubi, J-C., Laissue, J. A.; TIPS, 1995, 16, 110.
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Reubi, J.-C.1
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5
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0018770021
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4. For some interesting examples, see: (a) Veber, D. F., Holly, F. W., Nutt, R. F., Bergstrand, S. J., Brady, S. F., Hirschmann, R., Glitzer, M. S., Saperstein, R.; Nature, 1979, 280, 512.
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Veber, D.F.1
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Brady, S.F.5
Hirschmann, R.6
Glitzer, M.S.7
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(b) Nutt, R. F., Veber, D. F., Saperstein, R.; J. Am. Chem. Soc., 1980, 102, 6539.
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Nutt, R.F.1
Veber, D.F.2
Saperstein, R.3
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7
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0019862208
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(c) Veber, D. F., Freidinger, R. M., Perlow, D. S., Strachan, R. G., Nutt, R. F., Arisen, B. H., Homnick, C., Randall, W. C., Glitzer, Saperstein, R., Hirschmann, R.; Nature, 1981, 292, 55.
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Veber, D.F.1
Freidinger, R.M.2
Perlow, D.S.3
Strachan, R.G.4
Nutt, R.F.5
Arisen, B.H.6
Homnick, C.7
Randall, W.C.8
Glitzer9
Saperstein, R.10
Hirschmann, R.11
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8
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0023751786
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(d) Elseviers, M., Van Der Auwera, L., Pepermans, H., Tourwé, D., Van Binst, G.; Biochemical and research Communication, 1988, 154, 515.
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Elseviers, M.1
Van Der Auwera, L.2
Pepermans, H.3
Tourwé, D.4
Van Binst, G.5
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9
-
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0025895755
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(e) Spanevello, R. A., Hirschmann, R., Raynor, K., Reisine, T., Nutt, R. F.; Tetrahedron Lett., 1991, 32, 4675.
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Spanevello, R.A.1
Hirschmann, R.2
Raynor, K.3
Reisine, T.4
Nutt, R.F.5
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10
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0027085885
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(f) Huang, Z., He Ya-Bo, Raynor, K., Tallent, M., Reisine, T., Goodman, M.; J. Am. Chem. Soc., 1992, 114, 9390.
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Huang, Z.1
He, Ya.-Bo.2
Raynor, K.3
Tallent, M.4
Reisine, T.5
Goodman, M.6
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11
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0002404299
-
-
Rivier, J. E., Marshall, G. R., Eds; ESCOM, Leiden
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5. Original work was performed by Merck Research Laboratories [(a) Nicolaou, K. C., Salvino, J. M., Raynor, K., Pietranico, S., Reisine, T., Freidinger, R.M., Hirschmann, R., Peptides-Chemistry Structure and Biology: Proceedings of the Eleventh American Peptide Symposium; Rivier, J. E., Marshall, G. R., Eds; ESCOM, Leiden, 1990, 881.
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Nicolaou, K.C.1
Salvino, J.M.2
Raynor, K.3
Pietranico, S.4
Reisine, T.5
Freidinger, R.M.6
Hirschmann, R.7
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12
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0026470597
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(b) Hirschmann, R., Nicolaou, K. C., Pietranico, Salvino, J., Leahy, E. M., Sprengeler, P. A., Furst, G., Smith, B., Strader, C. D., Cascieri, A., Candelore, M. R., Donaldson, C., Vale, W., Maechler, L.; J. Am. Chem. Soc., 1992, 114, 9217.
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Hirschmann, R.1
Nicolaou, K.C.2
Pietranico3
Salvino, J.4
Leahy, E.M.5
Sprengeler, P.A.6
Furst, G.7
Smith, B.8
Strader, C.D.9
Cascieri, A.10
Candelore, M.R.11
Donaldson, C.12
Vale, W.13
Maechler, L.14
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13
-
-
0027857964
-
-
(c) Hirschmann, R., Nicolaou, K. C., Pietranico, S., Leahy, E. M., Salvino, J., Arison, B., Cichy, M. A., Spoors, P. G., Shakespeare, W. C., Sprengeler, P. A., Hamley, P., Smith, A. B., Reisine, T., Raynor, K., Maechler, L., Donaldson, C., Vale, W., Freidinger, R. M., Cascieri, M. R., Strader, C.D.; J. Am. Chem. Soc., 1993, 115, 12550]
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Hirschmann, R.1
Nicolaou, K.C.2
Pietranico, S.3
Leahy, E.M.4
Salvino, J.5
Arison, B.6
Cichy, M.A.7
Spoors, P.G.8
Shakespeare, W.C.9
Sprengeler, P.A.10
Hamley, P.11
Smith, A.B.12
Reisine, T.13
Raynor, K.14
Maechler, L.15
Donaldson, C.16
Vale, W.17
Freidinger, R.M.18
Cascieri, M.R.19
Strader, C.D.20
more..
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14
-
-
0026774922
-
-
and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C., Haltiner, R., Bruns C., Petcher, T.; Bioorg. Med. Chem. Lett., 1992, 2, 135.
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Papageorgiou, C.1
Haltiner, R.2
Bruns, C.3
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0030063814
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(e) Papageorgiou, C., Borer, X.; Bioorg. Med. Chem. Lett., 1996, 6, 267].
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Papageorgiou, C.1
Borer, X.2
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16
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0023084833
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and references cited therein
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6. Moreau, J. P., DeFeudis, F. V.; Life Sciences, 1987, 40, 419 and references cited therein.
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Moreau, J.P.1
DeFeudis, F.V.2
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17
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0018073512
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7. (a) Vale, W., Rivier, J., Ling, N., Brown, M.; Metabolism, 1978, 27, 1391.
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Metabolism
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Vale, W.1
Rivier, J.2
Ling, N.3
Brown, M.4
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18
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0023108388
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(b) Elst, V., Van der Berg, E., Pepermans, H., Auera, V., Zeeuws, R., Tourwé, D., Van Binst, G.; Int. J. Pept. Protein Res., 1987, 29, 318.
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Elst, V.1
Van Der Berg, E.2
Pepermans, H.3
Auera, V.4
Zeeuws, R.5
Tourwé, D.6
Van Binst, G.7
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19
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0029007817
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(c) Hocart, S. J., Reddy, V., Murphy, W. A., Coy, D. H.; J. Med. Chem., 1995, 38, 1974.
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Hocart, S.J.1
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Coy, D.H.4
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20
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-
0027085885
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-
8. Huang, Z., He, Ya-Bo, Raynor, K., Tallent, M., Reisine, T., Goodman, M.; J. Am. Chem. Soc., 1992, 114, 9390.
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, vol.114
, pp. 9390
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-
Huang, Z.1
He, Ya.-Bo.2
Raynor, K.3
Tallent, M.4
Reisine, T.5
Goodman, M.6
-
21
-
-
85030209038
-
-
note
-
1H Nuclear Magnetic Resonance spectra were recorded on DMX 600MHz (Brüker) spectrometer.
-
-
-
-
22
-
-
85030200498
-
-
note
-
(b) INSIGHT\DISCOVER PACKAGES (Biosym-Technologies Inc., 10065 Barnes Canyon Rd, San Diego, CA 91121, USA). Details of these data will be reported elsewhere.
-
-
-
-
23
-
-
0029137991
-
-
10. Pohl, E., Heine, A., Sheldrick, G. M., Dauter, Z., Wilson, K. S., Kallen, J., Huber, W., Pfäffli, P.; Acta Cryst., 1995, D51, 48.
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Pohl, E.1
Heine, A.2
Sheldrick, G.M.3
Dauter, Z.4
Wilson, K.S.5
Kallen, J.6
Huber, W.7
Pfäffli, P.8
-
24
-
-
0021854984
-
-
and references cited therein
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11. Wynants, C., Van Binst, G., Loosli, H. R.; Int. J. Pept. Protein Res. 1985, 25, 622 and references cited therein.
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Wynants, C.1
Van Binst, G.2
Loosli, H.R.3
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25
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-
85030204020
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French Patent application # 95 05510
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12. Damour, D., Depezay, J-C., Le Merrer, Y., Mignani, S., Pantel, G., Poitout, L.; French Patent application # 95 05510.
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Damour, D.1
Depezay, J.-C.2
Le Merrer, Y.3
Mignani, S.4
Pantel, G.5
Poitout, L.6
-
26
-
-
0029983723
-
-
13. For precedents on isomerization of polyhydroxylated piperidines, see: Poitout, L.; Le Merrer, Y.; Depezay, J-C.; Tetrahedron Lett., 1996, 37, 1609.
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Poitout, L.1
Le Merrer, Y.2
Depezay, J.-C.3
-
27
-
-
85030210433
-
-
note
-
14. The piperidine III can be obtained in better yield from the azepane 3b by treatment with mesylchloride to give 10b (60% yield, for analogous ring contraction, see ref. 15), and subsequent nucleophilic substitution with N-Boc-1,6-hexyldiamine (86%).
-
-
-
-
28
-
-
0029875649
-
-
15. For precedents on isomerization of polyhydroxylated azepanes, see: Poitout, L.; Le Merrer, Y.; Depezay, J-C.; Tetrahedron Lett., 1996, 37, 1613.
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Poitout, L.1
Le Merrer, Y.2
Depezay, J.-C.3
-
30
-
-
85030201609
-
-
note
-
17. The formation of these bridged compounds can be interpreted as an intrmolecular displacement of the mesylate by the cyclic nitrogen atom to give an aziridinium intermediate, the nucleophilic opening of which gives rise to the formation of two isomers with a piperidine or an azepane skeleton, followed by an intramolecular displacement of the remaining mesylate by the secondary amine, see ref 15.
-
-
-
-
31
-
-
85030199626
-
-
note
-
13C-NMR, MS) in accord with the assigned structure, and satisfactory combustion analysis or accurate mass measurement.
-
-
-
-
32
-
-
0000127560
-
-
50 values which are the mean of at least three determinations each with six concentrations of the test compound in triplicate.
-
50 values which are the mean of at least three determinations each with six concentrations of the test compound in triplicate.
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(1981)
Proc. Natl. Acad. Sci. USA
, vol.78
, pp. 3930
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-
Srikant, C.B.1
Patel, Y.C.2
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